For me, these topics seem extremely contextual and variable with the situation and specifics of the tradeoff in the moment. For many of them, I do somewhat frequently explore consciously what it might feel like (and for cheap ones, try out) to make a different tradeoff, but those experiments don't generalize well.
I suspect that for the impactful ones (heavily repeated or large), your first two bullet points don't apply - feedback is delayed from the decision, and if harmful, it will be significant.
Still, it's VERY GOOD to be reminded that these decisions are mostly made by type-1 thinking, out of habit or instinct (aka deep/early learning) that deserves reconsideration from time to time.
People behave differently from one another on all manner of axes, and each person is usually pretty consistent about it. For instance:
These are often about trade-offs, and the best point on each spectrum for any particular person seems like an empirical question. Do people know the answers to these questions? I’m a bit skeptical, because they mostly haven’t tried many points.
Instead, I think these mostly don’t feel like open empirical questions: people have a sense of what the correct place on the axis is (possibly ignoring a trade-off), and some propensities that make a different place on the axis natural, and some resources they can allocate to moving from the natural place toward the ideal place. And the result is a fairly consistent point for each person. For instance, Bob might feel that the correct amount to worry about things is around zero, but worrying arises very easily in his mind and is hard to shake off, so he ‘tries not to worry’ some amount based on how much effort he has available and what else is going on, and lands in a place about that far from his natural worrying point. He could actually still worry a bit more or a bit less, perhaps by exerting more or less effort, or by thinking of a different point as the goal, but in practice he will probably worry about as much as he feels he has energy for limiting himself to.
Sometimes people do intentionally choose a new point—perhaps by thinking about it and deciding to spend less money, or exercise more, or try harder to listen. Then they hope to enact that new point for the indefinite future.
But for choices we play out a tiny bit every day, there is a lot of scope for iterative improvement, exploring the spectrum. I posit that people should rarely be asking themselves ‘should I value my time more?’ in an abstract fashion for more than a few minutes before they just try valuing their time more for a bit and see if they feel better about that lifestyle overall, with its conveniences and costs.
If you are implicitly making the same choice a massive number of times, and getting it wrong for a tiny fraction of them isn’t high stakes, then it’s probably worth experiencing the different options.
I think that point about the value of time came from Tyler Cowen a long time ago, but I often think it should apply to lots of other spectrums in life, like some of those listed above.
For this to be a reasonable strategy, the following need to be true:
I don’t actually follow this advice much. I think it’s separately hard to notice that many of these things are choices. So I don’t have much evidence about it being good advice, it’s just a thing I often think about. But maybe my default level of caring about things like not giving people advice I haven’t even tried isn’t the best one. So perhaps I’ll try now being a bit less careful about stuff like that. Where ‘stuff like that’ also includes having a well-defined notion of ‘stuff like that’ before I embark on experimentally modifying it. And ending blog posts well.